Intramolecular iron-catalyzed transannulation of furans with O-acetyl oximes: synthesis of functionalized pyrroles
Literature Information
Anton S. Makarov, Alexander A. Fadeev, Maxim G. Uchuskin
Furyl-tethered O-acetyl oximes undergo a rearrangement to yield densely substituted pyrroles in the presence of FeCl3·6H2O. The reactivity of a furan ring resembles the behaviour of an activated olefin with a formal leaving group that reacts with electrophilic nitrogen in a 5-exo-trig manner to form a spiropyrroline intermediate followed by aromatization of pyrrole via an intermediate ring opening. In contrast to the common activation modes of O-acyl oximes that comprise homolysis, SET-reduction or oxidative addition of low-valent transition metal complexes across the N–O bond, in the present case the catalyst acts as a Lewis acid activating oxime nitrogen for a nucleophilic attack by the reaction partner. The studied reaction was integrated into a telescoping protocol for the synthesis of a broad range of pyrroles, which could find possible applications as flexible matrices for designing push–pull chromophores and as potential building blocks in organic chemistry.
Related Literature
Effect of temperature and packaging materials on the shelf-life stability and in vitro properties of microencapsulated and spray-dried synbiotic legume-based instant beverage powder
Smriti Chaturvedi, Snehasis Chakraborty
DOI: 10.1039/D3FB00094J
Recovery of palladium from waste fashion items through food waste by-products
Teresa Cecchi, Zhaojing Gao, Christophe Clement, Yasser Matos Peralta, Olivier Girard, Clara Santato
DOI: 10.1039/D3SU00242J
Al(iii)-based MOF for the selective adsorption of phosphate and arsenate from aqueous solutions
Herlys Viltres, Valeria B. López-Cervantes, Camilo Serrano-Fuentes, Amin Reza Rajabzadeh, Seshasai Srinivasan, Ricardo A. Peralta, Carolina Leyva
DOI: 10.1039/D3LF00061C
Sustainable production of prodigiosin from rice straw derived xylose by using isolated Serratia marcescens (CMS 2): statistical optimization, characterization, encapsulation & cost analysis
Kanika Miglani, Saumya Singh, Devendra Pratap Singh, Meena Krishania
DOI: 10.1039/D3FB00100H
Effect of chloride salts and microwaves on polyethylene terephthalate (PET) hydrolysis by iron chloride/acetic acid Lewis/Brønsted acidic deep eutectic solvent
Marco Rollo, Massimo A. G. Perini, Alessandro Sanzone, Lorenzo Polastri, Matteo Tiecco, Alejandro Torregrosa-Chinillach, Elisa Martinelli, Gianluca Ciancaleoni
DOI: 10.1039/D3SU00205E
Evaluation of the bioprotective potential of gastrointestinal digest fractions of Arthrospira sp. and Nannochloropsis sp. suspensions treated with high pressure homogenisation
Biniam Kebede
DOI: 10.1039/D3FB00193H
Interactions between liquid ammonia and graphitic materials
Cheng-Wei Lin, Zhiyin Yang, Ailun Huang, Xueying Chang, Chenxiang Wang, Fan Yang, Chen Wei, Markus Thiel, Yuto Katsuyama, Lihua Jin
DOI: 10.1039/D3LF00194F
Use of machine learning for monitoring the growth stages of an agricultural crop
Shara Ahmed, Nabanita Basu, Catherine E. Nicholson, Simon R. Rutter, John R. Marshall, Justin J. Perry, John R. Dean
DOI: 10.1039/D3FB00101F
Effects of different microwave power on the drying kinetics and physicochemical quality of brown shrimp (Metapenaeus dobsoni)
Sumit Kumar Verma, Remya Sasikala, Pankaj Kishore, C. O. Mohan, P. Ganesan, Pandurengan Padmavathy, Nagarajan Muralidharan, Bindu Jaganath, Soottawat Benjakul
DOI: 10.1039/D3FB00144J
You might also like
What industries use (1R,3S)-1,3-Cyclopentanediol (CAS: 16326-97-9)?
(1R,3S)-1,3-Cyclopentanediol finds applications in various industries. In the ph...
What precautions should be taken when handling N'-[4-(Dimethylamino)phenyl]-N,N-dimethyl-1,4-benzenediamine (CAS: 637-31-0)?
When handling N'-[4-(Dimethylamino)phenyl]-N,N-dimethyl-1,4-benzenediamine, it i...
Are there alternatives to 5-(2,4-Difluorophenyl)-2-methoxypyrimidine (CAS: 1352318-16-1) in synthesis?
There are several alternatives to 5-(2,4-Difluorophenyl)-2-methoxypyrimidine in ...
What regulatory guidelines apply to 1-(3-Methoxyphenoxy)propan-2-ol (CAS: 382141-68-6)?
1-(3-Methoxyphenoxy)propan-2-ol (CAS: 382141-68-6) must comply with the Globally...
Is Tetrodotoxin Citrate (CAS: 18660-81-6) safe?
Tetrodotoxin Citrate is extremely dangerous and should be handled with extreme c...
What are the main uses of 2-Methyl-2-propanyl [(1R,3S)-3-hydroxycyclopentyl]carbamate (CAS: 225641-84-9)?
2-Methyl-2-propanyl [(1R,3S)-3-hydroxycyclopentyl]carbamate (CAS: 225641-84-9) i...
How should waste containing 4-(2-Hydroxyhexafluoroisopropyl)Benzoic Acid (CAS: 16261-80-6) be handled?
Waste containing 4-(2-Hydroxyhexafluoroisopropyl)Benzoic Acid (CAS: 16261-80-6) ...
How is 2-Methyl-2-proanyl {(2S)-1-[(benzyloxy)amino]-3-hydroxy-3-methyl-1-oxo-2-butanyl}carbamate (CAS: 102507-19-7) typically synthesized?
2-Methyl-2-proanyl {(2S)-1-[(benzyloxy)amino]-3-hydroxy-3-methyl-1-oxo-2-butanyl...
What is Benzeneethanamine, α-ethyl-, hydrochloride (1:1) (CAS: 20735-15-3)?
Benzeneethanamine, α-ethyl-, hydrochloride (1:1) is an organic compound with the...
Are there alternatives to 3-{(E)-[4-(Dimethylamino)phenyl]diazenyl}benzoic acid (CAS: 20691-84-3) in synthesis?
In the synthesis of compounds similar to 3-{(E)-[4-(Dimethylamino)phenyl]diazeny...
Source Journal
Organic Chemistry Frontiers

Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry














